tagAnalWeekends with an Anal Lover

Weekends with an Anal Lover


I had been divorced for about a year before I went to my first singles get together. It was held at a local bar and restaurant in town. The bar was closed to others and only those that attended the singles meeting were allowed in. I did not know what to expect since I had never been to one of these meetings, however I needed a break from the normal bar scene.

When I first arrived I checked out everyone that was there. They all seemed to be older than my 35 years and most of them were out of shape. It was disappointing to see so many unfit people in their 30's and 40's. Then I spotted one woman who looked younger and fitter than any others. I walked over to her and introduced myself.

"Hi my name is Walt."

"Hi I'm Bonnie," she replied with a smile and then asked, "Is this your first time at one of these meetings?"

"Yes it is. How do they normally go," I asked in reply.

"This is only my second meeting but it will probably be my last. People just sit around talk, drink and dance occasionally. The people are pretty boring," Bonnie admitted.

"I was surprised when I looked around that you were here as you don't seem to fit in," I told her.

"Why do you say that?' she asked.

"Well you are younger and fitter than the others for starters."

"Thanks for noticing, you are too," Bonnie said with a smile.

"Would you like to go somewhere else? Have you had dinner yet? We could go to diner if you like," I offered.

"Maybe a burger, I'm not that hungry," she accepted.

Bonnie and I left the singles party to get a burger at her favorite burger restaurant. As she walked out in front of me I took a closer look at her figure. She was about 5'6" and I guessed her weight to be about 115 pounds. She was small breasted with a narrow waist that flared out into wider hips. She was wearing a loose fitting skirt so it was hard to assess her legs and her ass. Bonnie had blonde hair that was coarse in nature so she kept in short. We drove separately to the restaurant where we had a pleasant meal and engaging conversation.

Over dinner I learned that Bonnie was also divorced for just over a year. She worked as and Admin Assistant for an Executive at a local insurance company. She took good care of herself as she worked out five days a week, three of those days doing aerobics. I also took good care of myself as I trained at the gym and I was taking a class in martial arts. Bonnie was pleased to hear that I also played tennis, golf, snow skied and SCUBA dived. She told me that she liked active and fit people. I was happy to hear that as I was proud of my 6'2", 190 pound physique.

We also shared that both our divorces were no fault and clean breaks. My former wife and I just agreed that we didn't want to be together after 10 years of marriage and Bonnie had a similar situation. We finished our meal and then we agreed to go out together the next weekend. I asked Bonnie if she would like to go to a show and dinner and she accepted. I told her that there was a play I wanted to see downtown and she agreed to go with me. We said goodnight and then drove home to our respective condos.


The next Friday evening I picked up Bonnie at her condo. She lived in an interesting community as all the condos were detached and really looked like small house close together. My condo community was much different as I had opted for the amenities of a club house, fitness center and swimming pool.

Bonnie was dressed very different that evening as she wore a tight mini skirt that showed off her shapely legs and very curvy ass. Bonnie had a true bubble butt and it was one of those asses that you always wanted to touch when close to it. I felt my loins stir at the sight of her. I opened the car door for her and she slid into the seat. As she did her skirt rode up and I noticed the elastic tops of her hose. By the time I walked around the car to the driver's side I could feel my cock hardening in my pants. As I drove to the theater I kept glancing over at Bonnie's legs as her skirt barely covered the tops of her hose. I was sure that she saw me checking out her legs as she smiled at me several times.

The play was very entertaining and we had an excellent dinner afterward. I was amused at the number of guys, even those with dates, who checked out Bonnie when she walked by. I knew that they were all checking out her great ass. After dinner I drove Bonnie back to her condo and up until then we had not shared any signs of affection toward each other. I pulled into her driveway and I hoped that she would ask me in for a nightcap.

I turned toward Bonnie and she smiled at me. I leaned in toward her and kissed her and she kissed me back. Within minutes we were kissing each other deeply and our tongues explored each other's mouth. I had an immediate erection that was straining to get out of my briefs. I pulled Bonnie to me and her skirt rode up over her hose baring her luscious thighs. I reached down and stroked the bare skin of her thighs as I kissed her. Bonnie responded by feeling for my crotch. She located my erect cock and she rubbed it through my pants. We continued to kiss and fondle each other driving each other crazy.

As we kissed Bonnie managed to unzip my fly and free my cock. She pulled my briefs to one side so that my cock and balls were free. She took hold of my cock and stroked it as we kissed and I caressed her thighs. I tried to get my hand inside her panties but she moved away. At first I was disappointed but hen she lowered her head to my lap and engulfed my cock in her mouth. Bonnie sucked on my cock and I instantly knew that she was a very accomplished cock sucker. I groaned loudly as she deep throated my 7+ inch cock and fondled my balls in her delicate hand. I was sure that she was going to let me cum in her mouth.

Just before I came Bonnie lifted her head off my cock and asked, "Would you like to come inside?"

What a question. Here I was ready to blow my load into her mouth when she stops and asks me in. I sat there speechless for a moment as she stroked my cock lovingly. Then I answered her in a shaky voice.

"I would love to come inside. I can't possibly stay here in this condition," I stammered.

Bonnie just smiled at me and then straightened her skirt before opening the car door. I quickly pushed my cock back onto my pants and zipped up before I got out of the car. We walked up to her front door and I looked at her shapely ass again. I wondered if she liked anal sex. She definitely had an ass that I would love to fuck but I had learned not to push it. Bonnie let us in the condo and from there we went straight to her bedroom where we undressed and got into to bed naked.

Bonnie was ready as was I so there was no need for additional foreplay. I slipped right between her thighs and my cock slid into her wet pussy like a hot knife through butter. Bonnie moaned as my cock entered her cunt and she wrapped her arms and legs around me as I went deep into her. We fucked slowly at first and then picked up the pace. Bonnie had a mild orgasm along the way to a massive one. Her body rocked and gyrated as she screamed in ecstasy and it was all I could do to hold on as she bucked up at me. Then I felt my surge and I drilled deep into her pussy just before I unleashed a massive cum load. I felt my cum shoot out of my cock deep into her womb and Bonnie held me tighter as I came in her.

We stayed together for several minutes with my cock buried deep in her pussy and her arms and legs still holding me tight. Bonnie and I separated and I rolled over on my back. She surprised me when she moved back down and took my cock in her mouth. Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Bonnie moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole wet enough with her juices and my saliva so that I could fuck her ass.

I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My cock is 7-8 inches long and about 5' around. There are times when it feels bigger and this was one of those times. I was fingering Bonnie's ass when she spoke.

"You are going to need some cream. There is some in my bathroom" she whispered.

I got off the bed to retrieve the lotion from the bathroom. As I did I realized that Bonnie was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Bonnie moaned as my penis filled her hole.

"Go slowly at first it has been awhile," she said sexily.

I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my penis move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear.

"Bonnie you have a hot ass, I love fucking you in your hot ass."

My hands freely roamed her body and I pulled her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Bonnie's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Bonnie felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Bonnie writhed around and her body arched off the bed as a climax of massive proportion tore through her loins.

My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me again when she covered my cock with her mouth and sucked any remaining cum from my tool. Bonnie then lay on her back, splayed her legs and pulled back the folds of her vagina.

"Here eat my pussy, please eat my pussy," she pleaded.

I rolled over and got between her legs and blocked out that fact that I had cum in her before. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Bonnie's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Bonnie enjoyed it. I enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice. Soon I was like a puppy at a saucer of milk, licking and lapping up as much as I could as fast as I could.

Bonnie was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. My tongue explored all of her as my mind took notes of what seemed to turn her on. Bonnie was breathing rapidly and she moaned softly whenever I got near her hard pearl. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched that pearl.

I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her pearl I used the very tip of my tongue to push back the little hood. I was truly amazed at its size. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Bonnie was now moaning and she used her fingers to pull her hood back as she arched herself so that her pearl stuck out even further like a little cock. I nuzzled it with my nose taking in her scent and I licked it once more before I took it between my teeth and gently nibbled it.

Bonnie went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Bonnie humped my face for all she was worth. I was thrilled that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Bonnie came but finally she collapsed on the bed, her body in spasms.

I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight.

"Hold me, oh please hold me," she pleaded as her orgasm and spasms continued.

I had never seen anyone cum that hard before and I was briefly worried that she had injured herself. My fears were short lived when she finally calmed down and spoke to me.

"That was incredible I haven't cum like that in a long time. You really know how to eat pussy," she said with a sigh.

We lay there for awhile making small talk and then Bonnie started stroking my cock. Now at the age of 36 it was very unusual for me to cum more than twice in a fuck session, particularly after having a couple of drinks. In fact I usually could stay hard for a long time before my second cum which allowed me to pleasure my partner thoroughly before achieving my own orgasm. Bonnie added some body lotion as she kept stroking my cock and soon had me hard again.

"I like playing with your cock. You have a big cock," she told me.

"It's not that big," I replied although I was very comfortable with me manhood.

"It's bigger than my ex-husband's and the biggest I have ever had," she said with a sultry tone.

"Well there are plenty bigger than mine," I assured her.

We continued our conversation as Bonnie continued to stroke my cock. I learned that she had first been ass fucked before she was married. Bonnie was working in Washington, D.C. at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. Her ex-husband did not like butt fucking and he also had lost interest in eating pussy, so for them it was straight sex. She also told me that this was the first time she had anal sex with anyone since her divorce. I shared with her that I loved fucking a beautiful ass but that my ex-wife did not like anal sex and she didn't like sucking cock either.

"All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced.

Bonnie straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Bonnie rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. Bonnie started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out.

"I am going to explode. Oh, Oh hold me, please hold me tight," she screamed.

Bonnie collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me.

"Can you stay with me tonight?" she asked in a sultry tone.

"I would love to stay the night with you," I told her.


Saturday morning I woke up with Bonnie stroking my cock. She smiled at me when she saw I was awake and then she lowered her mouth to my cock and deep throated me as she had the night before. I had a tremendous urge to piss but I knew I couldn't as long as my cock was hard and I couldn't cum until I took my morning piss. I decided then to fuck Bonnie into submission that morning. I rolled her over and got on top of her and slipped my early morning erection into her moist pussy. I started fucking her slowly and gradually picked up the pace as she moaned and groaned with desire. Bonnie did not know what she was in that morning and I was determined to fuck her brains out. I could fuck for a long time without cumming the first in the morning with my piss hard-on. As I pounded Bonnie's pussy she had a continuous string of orgasms. She was screaming and thrashing in ecstasy. Bonnie held me tight, dug her heels into my back and muffled her screams in my shoulder as I pounded her pussy. Finally she shook uncontrollably, screamed and collapsed, her body going limp on the bed.

"Please stop fucking me, no more please. I can't cum anymore please let me rest," Bonnie pleaded.

I eased my still hard cock out of her cunt and I actually heard her pussy sucking as if it was gasping for air. I slid off the bed and went into the bathroom to take my morning piss. When I returned to the bedroom Bonnie was in the same position that I had left her. I got back in bed and rolled her over on her stomach.

"Please Walt let me rest awhile," Bonnie begged.

"Relax and I will give you a massage," I told her.

I took the lotion from the night table and applied it to her back and shoulders. I massaged her neck, shoulders and back rubbing the lotion in and relaxing her body. Then I moved down to her calves and massaged her aching legs. I worked my way up to the back of her thighs and massaged them deeply. Bonnie moaned and cooed under the manipulation of my hands and I knew that she was enjoying the massage. I next moved my hands to her buttocks and massaged her glutes as I knew they were fatigued from all of our fucking the past two days. Bonnie involuntarily tightened her butt muscles as I massaged them and I felt my cock get hard again.

I put more lotion on Bonnie's ass and worked some of it into her crack. Bonnie raised her ass slightly and I slipped a lubed finger into her bung hole. Bonnie gasped at the intrusion but then relaxed and enjoyed the stimulation. I added a second finger and Bonnie gasped again. As I worked my two fingers in her ass my cock had become fully erect again. I lifted Bonnie by her hips and she allowed me to lift her ass higher as she kept her head on the bed. I was sure that she knew I was going to take her ass again and she offered no protest.

I lined my throbbing cock up at the entrance to her ass and pushed it in until the head cleared her sphincter. Once again Bonnie gasped at the intrusion but she did not resist. I eased my cock into her ass inch by inch until it was completely buried in her anal channel. I started slowly as I had before and then picked up the pace. Watching Bonnie's ass impaled on my cock as I fucked her sent a chill through my body. My own orgasm, the first one of the day, was building in my balls and I knew it would be a matter of minutes before I ejaculated.

My body stiffened, my balls tightened and the first stream of cum entered Bonnie's asshole catching her by surprise. I pulled my cock from her ass as I continued shooting cum at her asshole. My semen bounced off her anus and her buttocks and then ran down over her pussy lips onto the bed sheets. After shooting my last stream at her aperture I shoved my cock back into her ass. Bonnie once again milked my cock with her anal muscles and drained it dry. My cock stayed hard and I was sure that I could fuck her again but we had the whole day ahead of us and I withdrew my cock from her ass. Cum bubbled from her butt hole and trickled down over her vulva. There was more cum this time since I had shot my first load deep into her rectum. Bonnie worked her muscles and squeezed the semen from her ass as I watched.

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